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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Featured Cottages in Winter Garden and around

Orlando Lakefront Tiny House Community
The Sunshine Lake Shake

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (330)
"We enjoyed our stay."
Orlando Lakefront Tiny House Community
8000 Lost Shaker Lane
Miscellaneous

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"Great place! good location and clean but the patio furniture looked like a hurricane had just happened. I try calling the company incharge of the rental unit but they never came to fix it. Overall good place to stay! "
8000 Lost Shaker Lane
Cozy Cottage 3 blocks from town
Exterior

Cozy Cottage 3 blocks from town

10.0 out of 10, Exceptional, (37)
"Great place close to everything would definitely stay again"
Cozy Cottage 3 blocks from town
ADorable Downtown Mount Dora Cottage with Fenced Yard for your pet
Exterior

ADorable Downtown Mount Dora Cottage with Fenced Yard for your pet

9.8 out of 10, Exceptional, (35)
"Great location. "
ADorable Downtown Mount Dora Cottage with Fenced Yard for your pet
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.2 out of 10, Wonderful, (51)
"We had such a great time staying here. A cute little spot made a great quick stay for us."
The price is €127
includes taxes & fees
5 Oct - 6 Oct
Tiny Hidden Cottage
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Property grounds

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

10.0 out of 10, Exceptional, (4)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
The price is €219
includes taxes & fees
6 Oct - 7 Oct
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Oaktree Cottage in Mount Dora Historic District
Exterior

Oaktree Cottage in Mount Dora Historic District

9.8 out of 10, Exceptional, (10)
"Tastefully decorated and well equipped rental. Convenient walk to downtown "
Oaktree Cottage in Mount Dora Historic District
Mount Dora Cottages
Front of property

Mount Dora Cottages

3.0 star property
9.4 out of 10, Exceptional, (208)
"Our family loved this place and the neighborhood is perfect for a quiet afternoon. "
The price is €202
includes taxes & fees
5 Oct - 6 Oct
Mount Dora Cottages
Family 4BR Home w/ Resort Pool Near Disney
House (4 Bedrooms) | Floor plan

Family 4BR Home w/ Resort Pool Near Disney

3.0 star property
Family 4BR Home w/ Resort Pool Near Disney
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

10.0 out of 10, Exceptional, (28)
"Easy and convenient in a nice place "
The price is €307
includes taxes & fees
6 Oct - 7 Oct
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
5003 Windermere Avenue
Miscellaneous

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (3)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
Outdoor spa tub

LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando

10.0 out of 10, Exceptional, (179)
"Had a great time. Very cute home on a relaxing lake. Hosts very helpful and communicative. Wish we could have stayed longer. "
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
End of the summer special! Guesthouse with lake view and private pool
Exterior

End of the summer special! Guesthouse with lake view and private pool

9.8 out of 10, Exceptional, (42)
"Really happy with our choice to stay here. The house was perfectly clean and comfortable, the kitchen is well equipped, the pool was amazing and felt private and relaxing. This will be my top choice to book again next time I am in the area. "
The price is €235
includes taxes & fees
12 Oct - 13 Oct
End of the summer special! Guesthouse with lake view and private pool
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Exterior

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

10.0 out of 10, Exceptional, (139)
"Everything was stellar!! Loved Mt Dora!! Loved the location. "
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
Terrace/patio

Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome

2.0 star property
10.0 out of 10, Exceptional, (15)
"Great place to stay very clean and warm loved it would recommend "
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Outdoor dining

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Exterior

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Downtown Cottage

8.4 out of 10, Very good, (6)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
The price is €159
includes taxes & fees
12 Oct - 13 Oct
Downtown Cottage
Modern Townhome W/private Pool & Free Water Park!
Miscellaneous

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"Place was in great location. "
Modern Townhome W/private Pool & Free Water Park!
Historic Tremain Cottages
Front of property

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very good, (31)
"Great location!"
Historic Tremain Cottages
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Garden Hotel Reviews

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

10/10 Excellent
"Great breakfast, helpful and kind staff."
Mara 6-night trip
Posted 1 day ago
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Find out more about Winter Garden

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
1,125
Accommodation
1993 Cottages
Lowest Price
€127
Highest Price
€307

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between €127 and €307 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodation that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.